One of the oddest things that used to happen to me often... not so much today, was that from 1970 until 1972 I was out of the country - and had no, or at least very little, access to the radio hits during that time. Meaning:
For some years after that I'd hear a song thinking it was new... relay that information to family and friends only to discover it was an old hit that came out when I was out of the country.
But as for missing artists... some of that I think due to my tendency in those days to stick with one genre for quite a while... so if I was into R&B I would hear little country, pop, classical, etc. Also, it took me a very long time to give country & western a chance, I didn't like it. My turn-around wasn't quick, either... it took several years... almost like one song at a time. Today I love it.
But it's great, isn't it? To discover an artist you missed, even if from decades ago. As good as hearing something new for the first time, I think. - JamesJM